Quantitative determination of singlet oxygen. Production by porphyrins

Kreitner, M.; Ebermann, Robert; Alth, G

doi:10.1016/s1011-1344(96)07356-3

Cited by 12 publications

(2 citation statements)

References 13 publications

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“…These compounds are highly reactive toward O 2 ( 1 D g ), but there are some limitations, they can react with other oxidants. 38 In biological systems cholesterol is considered as a fingerprint of O 2 ( 1 D g ) oxidation. This chemical trap has low rate constant of O 2 ( 1 D g ) (k r = 8 ¥ 10 4 M -1 s -1 ) quenching and the formed product is not stable and can undergo rearrangement.…”

Section: Photophysical Analysismentioning

confidence: 99%

Singlet molecular oxygen trapping by the fluorescent probe diethyl-3,3′-(9,10-anthracenediyl)bisacrylate synthesized by the Heck reaction

Oliveira

Severino

Prado

et al. 2011

Photochem Photobiol Sci

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Singlet molecular oxygen O(2)((1)Δ(g)) is a potent oxidant that can react with different biomolecules, including DNA, lipids and proteins. Many polycyclic aromatic hydrocarbons have been studied as O(2)((1)Δ(g)) chemical traps. Nevertheless, a suitable modification in the polycyclic aromatic ring must be made to increase the yield of O(2)((1)Δ(g)) chemical trapping. With this goal, an anthracene derivative, diethyl-3,3'-(9,10-anthracenediyl)bisacrylate (DADB), was obtained from the reaction of 9,10-dibromoanthracene and ethyl acrylate through the Heck coupling reaction. The coupling of ethyl acrylate with the anthracene ring produced a new lipophilic, esterified, fluorescent probe reactive toward O(2)((1)Δ(g)). This compound reacts with O(2)((1)Δ(g)) at a rate of k(r) = 1.69 × 10(6) M(-1) s(-1) forming a stable endoperoxide (DADBO(2)), which was characterized by UV-Vis, fluorescence, HPLC/MS and (1)H and (13)C NMR techniques. The photophysical, photochemical and thermostability features of DADB were also evaluated. Furthermore, this compound has the potential for great application in biological systems because it is easily synthetized in large amount and generates specific endoperoxide (DADBO(2)), which can be easily detected by HPLC tandem mass spectrometry (HPLC/MS/MS).

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Section: Photophysical Analysismentioning

confidence: 99%

Singlet molecular oxygen trapping by the fluorescent probe diethyl-3,3′-(9,10-anthracenediyl)bisacrylate synthesized by the Heck reaction

Oliveira

Severino

Prado

et al. 2011

Photochem Photobiol Sci

View full text Add to dashboard Cite

show abstract

“…Cisteínas foto-oxidadas levam à formação dos dissulfetos correspondentes, podendo em alguns casos formar também ácido cisteico (Langlois et al, 1986;Davies et al, 2004) Introdução A reação do 1 O 2 com aminoácidos em proteínas, com exceção do triptofano, variam consideravelmente uma vez que a ligação peptídica presente em di e poli peptídeos afeta consideravelmente a reatividade dos substituintes (Ronsein, 2008 (McCall, 1984). Por muito tempo, os captadores mais utilizados foram os derivados do furano (Kreitner et al, 1996) que são oxidados a produtos dicarbonílicos presumidamente via reação Diels-Alder para formar ozonida como intermediário. Embora os derivados de furano sejam altamente reativos com 1 O 2 , eles apresentam a desvantagem de reagir com outros oxidantes gerando os mesmos produtos observados pela reação com 1 O 2 (McCall, 1984).…”

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